The Undercover Detective Part 3 free porn video

The Undercover Detective Part3 19th May On the Saturday, I started my special leave. Kate was free for the weekend, as well, so it was ideal. After a leisurely breakfast, I started planning with Kate. "OK Kate, what are the ingredients of an instant lady outfit?" "First we need to decide what sort of woman you are going to be. Are you going to be demure, sexy, smart and fashionable, a total slapper or a shy little girl?" "Buggered if I know, what would you recommend?" "Do you want to pick up men on your first outing. Are you looking for a one night stand?" "For goodness sake, be serious." "So I take that as a no then. Let us try for smart and fashionable. Right a shopping list: 1. four pairs of nice knickers 2. two bras, preferably matching and padded. What chest are you, lets see if you can fit into a 38A 3. four pairs of hold up stockings, a darkish shade, not too fine 4. two dresses, preferably long sleeve and mid calf. Two skirts, two blouses, a T shirt and a sweater. 5. one half slip 6. a wig 7. some chicken fillets to fill the bra, or some breast forms 8. get your ears pierced and some pretty studs. Dangly ear rings will be needed, but you will have to wait for your ears to heal 9. at least two pairs of shoes to go with the dress. You are a man's seven, your best bet may be to buy mules. You may not be able to get courts to fit. You can get away with a tighter fit with mules 10. false nails to hide your tatty bitten ones 11. nail varnish 12. mascara 13. eye make up 14. foundation 15. a clutch bag 16. a purse 17. some jewellery including a couple of rings You can borrow one of my watches, a bracelet and a necklace. I don't think you will need a choker because your Adam's Apple does not stick out. We will need to get dresses at charity shops but the rest is going to need to be new." "Bloody hell, this is going to take ages." "Yes, and you do realise that we do not know your dress size, so you are going to have to try stuff on. I will take your chest measurement just to make sure you can fit a 38. Oh, I am going to have fun. One thing we need to look up on the net, is what to do with you cock and balls. It won't be ladylike for them to be sticking out." "I can't try on women's clothing in public." "You are going to be wearing women's clothing in public, so be a brave boy. I am going to have to get you used to wearing heels, sorting your wig out, doing your nails and putting make up on. We had better get the shopping done as soon as possible. Finish your breakfast and wash up while I find out where to get a wig." Our first port of call was the wig shop. We decided on a dark, almost black, wig, shoulder length at the back and a fringe at the front this was despite having auburn hair. I thought it would make me less recognisable. There was already a curl under at the shoulder. We did not pay the price of a human hair wig, but the one that we bought did not look too bad. Next it was M&S for knickers, pants, a half slip and stockings. The variety of styles was bewildering. A padded 38A bra was the choice. Once we had purchased those, Kate took us to a specialist shop and bought some silicon fillets to supplement the bra padding and bought a strange looking bit of material that she called a waist cinch. It was advertised for Postpartum, whatever that is. Next we started hitting the charity shops. This is where it got embarrassing. Kate would make it obvious that the dresses were for me, by holding them up against me and discussing whether I thought they would suit me. She reckoned that, if the material was stretchy, I might get away with a size 12 or 14. If it was not, then it would be a 14 or 16. In the third shop we found a dress in fine grey wool that had a high neck and came down below knee length. It had long sleeves and the material was stretchy. It was a 12 but seemed a generous 12. I thought it would do. Four more charity shops later, we had managed to find a pencil skirt with a shortish side slit, in black and a cream, long sleeved blouse. Kate then decided that I should get a camisole top to go under the blouse. We also found a black leather, clutch bag. The next visit was hugely embarrassing, it was to a shoe shop. Kate had me trying on all sorts of shoes. In the end we found a pair of black strappy sling backs with a one and a half inch heel. If the heel strap was on the furthest hole, I could get them on. I had some very funny looks from both customers and staff. We also found a pair of flat casual shoes in a brownish beige. The ear piercing would have been fine, except for Kate's choice of studs. She picked moonstones in a silver setting. There was nothing manly and butch about them. From that point on, I was going to look a bit odd. The make up was no problem, I just stood back and let Kate get on with it. The rings were a bit embarrassing, they had to be feminine and they had to fit me. I was becoming indifferent to looks and comments by this time. When we got home, the first thing I was told to do, was get rid of all the hair on my legs, pits, arms and hands. I also had to have a very close shave. Luckily, I do not have a heavy beard. Next, Kate decided to have a go at hiding my meat and two veg. We had found on the web, that with a bit of manipulation, it should be possible to push your testicles back up into the cavities from which they had descended years ago. Then, you taped your cock back into the crack of your arse and held it all together with a pair of tightish panties. The theory was good, but the more Kate tried to manipulate my tackle, the more aroused I got. In the end, we gave up and did what was coming naturally. Once we remembered what we were supposed to be doing, Kate tried again, this time with the assistance of some ice cubes. It was uncomfortable, but it worked. With the panties on, there was nothing male down below. Next, I found out what the cinch did. I had to wriggle it up my legs and over my bum. It the fitted round my waist. It strangled me, but it did pull my waist in a lot. It also pushed some of the surplus down to my hips. Next were the stockings, now they felt nice, I could get used to them. The bra fitted, just, and with the fillets inserted, I now had a bit of a bust as well as a waist. Next the slip and the grey dress, it fitted snugly. With the slip, I was not showing a very distinct visible panty line. Kate lent me a broad red belt to give a bit of colour. We then worked out how to secure the wig and Kate showed me how to brush it out and make it look presentable. The fun and games started in earnest then. Kate showed me how to put foundation on, she then wiped it off and made me do it several more times. That was the easy bit, when we started on eye make up it became painful. I found it extremely difficult to apply anything in a fine enough way to avoid looking like a clown. I also found it almost impossible to avoid poking myself in the eye. We spent two hours repeating the process over and over again until I pleaded for mercy. I was then given instruction in putting on lipstick and painting my nails. First I was made to tidy both fingers and toes with a nail file. The toes were done in one go, but the fingers involved some artificial nails to hide my raggity ones. Once all of that had been done, it was already early evening. We were both starving. Kate suggested that, now that I was dragged up, we could go out as a pair of women, for a meal. There was no way that I was going to agree to that. I might look, just about passable if I did not move or open my mouth, but as soon as I tried to do anything I looked like a bloke in drag. I needed to get the movement, mannerisms and voice, before I went out. We ordered a Chinese take away to be delivered and I agreed to go to the door, when it came. The young lad, that delivered it, never gave me a second look. Whilst we were eating, Kate kept pointing out how my mannerisms needed to change, if I was to convince anyone that I wanted to be seen as female. The rest of the evening we watched TV and my lessons in female behaviour continued. And so to bed, but only after I went through a cleansing and moisturising routine. Neither of us wore anything in bed so I did not have the indignity of a nightdress. 20th May I got up and got dressed in a different outfit, before bringing Kate breakfast In bed. The only thing that I had not managed, was putting my testicles and old man out of sight. I had even managed rudimentary make up. After Kate had enjoyed a leisurely start to the day, she amused herself by helping me crush my testicles back into their cavity. We started my tottering times as I practiced walking in heels. I also practiced talking in a female voice, or at least as close as I could get. Kate suggested going out together for lunch, but I would not consider it. We did go out, but only after I had changed back to male. To my embarrassment, I still had some traces of eye make up remaining and I had not cleaned all the nail varnish off my finger nails. On a couple of occasions, girls noticed and burst into fits of giggles. I even had a nice smile from a very openly gay man. When we got back to the flat, I had another practice at getting dressed and trying to appear female. By the time we were ready for bed, I was feeling a little more comfortable. 21st May morning I met up with DS Waters in a local coffee bar. "How did your shopping go?" "Pretty good. I think we have enough to make a start. We spent more than I expected, even though we bought cheap and, wherever possible, from charity shops. When we worked out what was necessary, even to manage just a few days, it was one hell of a lot. If I am going to spend a lot of time in drag, then I am going to need more. I need to think about the different contexts as well." "Now the boss and I have talked about where you should start and where your priorities should be. This evening, Sparkles will be awash with trannies and cross dressers, what we want you to do is to spend the evening, night and morning getting to know as many of them as possible. Try to find a way to get your feet under the table. Get involved as much as possible. Find out where they go other than Sparkles and go there. If you can find work in that crowd, do so. Make out that you might be interested in escort work. We need to find out as much as possible about who Frank Johns and Vickers mixed with, who were their friends, who did they have sex with. What men did they mix with? Where did they go, when in drag? Most of all, we need to find connections between the two. Start with them first. Someone has mixed with the two of them, and by the look of it, either had sex with them, or at least been aware of them having sex with men. Find out who fits the bill. Any person who looks to be of interest, let us know and we will follow it up. Get immersed in this weird world as quickly as possible. Be careful, and don't become victim number three. You will need to dig hard to find suspects. Contact me for an update every day." "How am I going to get into their world and find out about their sex lives?" "That is entirely up to you. It was your idea after all. Don't ask me to work it out for you." The rest of the day was spent worrying about my first night in drag, in public. 22nd May breakfast When I first woke up, I did not know where I was. It quickly dawned on me that I was in a room at Sparkles. My first question was, what do I do now. I had made a start, but I had not got very far. I needed to try to get myself more integrated into the scene. I thought that it may be possible to apply for a job at Sparkles, though that seemed unlikely. All the staff seemed to be extremely buff young men, not a tranny in sight. I would have to play it by ear. My first decision was to go to breakfast dressed in one of my other outfits. I managed to get my testicles into their cavities and taped my old man back. Next were the waist nipper, then knickers and bra and the chicken fillets then stockings, I liked putting them on. I checked my beard and, even though it was not showing, I gave it a close shave. Next was the slip, pencil skirt and blouse, by this time I was feeling trussed up again. Make up was my next task. I managed to put it on without looking like a clown. It was less heavy than the night before. My finger and toe nails were still a deep red. The wig and shoes completed my outfit, one last look in the mirror, pick up my handbag, a deep breath and out the door. When I got down to the restaurant, there were quite a few at breakfast. Some were dressed in female clothes, some in male and a couple, neither one thing or the other. I saw Aunty Mary just as she saw me. She was sitting with one other person, about my age, who was also dressed in women's clothes, but had a badly bruised face that she had tried to hide under make up. "Hi Mandy, come and join us. This is Sue, we have been discussing possible solutions to her problems. Lovely to see you dressed for breakfast and very pretty you look too. How did you enjoy your first night out as Mandy?" "It was scary and it was exciting and it felt like I had become me." "What are you going to do when you leave here today?" "I don't know, I was hoping that I could hang around here, Mac and Mabel's club opens for karaoke tonight." "Not possible, I am afraid, my love. The normal staff will be cleaning up, preparing for this evening and entertaining some special guests. We trannies are not wanted here during the day. Where is home?" "That is the problem. I got dressed as Mandy, and told my parents that I was coming here. They went mental, when they saw me, and told me not to come back, unless I promised never to dress as a girl ever again." "So what were you going to do?" "I don't know, I thought of getting a job and finding somewhere to stay. I have some savings and my small stash of clothing. I suppose, I will have to find somewhere to live and find some way of making money. I don't want to go back to being a boy, I want to live as a girl." "How much money have you got?" "A bit over ?1000 and some change. I have a credit card that has a ?3000 limit and it is currently clear." "That will not get you far. How old are you?" "21, I have just finished my finals. My friends have still got exams to take. I have not been able to find a proper job yet, I have been working in Debhenams at the weekends. The supervisor did not like me, because I would not give him a blow job. He said that it was a waste of time having a girly boy on the team if she did not play ball. I would rather not try to work there full time. I was wanting to start becoming more of a girl. I have left home now, but I don't know where to begin." "Goodness, I have just been deciding what to do about young Sue here and now you land on my plate, as well. As you can see, young Sue has taken a bit of a beating. She was thrown out by her parents, when they discovered that she had been self medicating on hormones and had been sneaking out dressed as a girl. She was seeing men at a bar in town and having sex with them. No harm in that as long as you are careful and sensible. When her parents threw her out, one of her men offered to put her up. For the last six months, he has been beating her and sharing her with his mates. She saw my little add, for shelter, and came to find me. I was just trying to decide what to do with her, now I have you to think about as well. Are you determined to transition, or do you just want to wear women's clothes and present as a woman?" "I think I want to transition. I know I want to live as a girl and I know that I would like to change my body to fit who I am." "Have you taken hormones?" "Not yet." "Have you had sex with men?" "Not really, when I was younger, I thought I might be gay, and played around with a gay boy from school. I didn't seem right. When I was at uni I lived at home, so opportunities were limited, but the last two Halloweens I managed to go out dressed and danced with guys, kissed them and thought about sucking them off, but didn't have the courage. I don't know about sex, I am a virgin and scared." "Sue here, is two years younger than you and has a lifetime of experience compared with you. Now I will tell you what I do. I have a big house, which can accommodate a lot more than me. I have been taking in young homeless cross dressers and the transgendered for some years. I have two businesses. I have a shop that caters for cross dressers, transsexuals and people who just like kinkyness. I also have a maid cleaning service. My maids are all or were originally men. They all present as females and dress in maids uniforms. The maids will do cleaning jobs and serving at functions. There is no sex involved. My clients know to leave my girls alone. Some girls make separate arrangements with clients, but that is up to them. I pay ?15 per hour for daytime work and ?25 per hour for evenings. Uniforms are provided. When girls have no home of their own, I will put them up and charge ?70 per week for full board. I usually get girls to share a room and you would be expected to share all the household chores. At the moment, I only have two other girls stopping, so you could have a room each, but I think it would be good for the two of you to share. I have contacts with psychiatrists and doctors, so I can help you on your way. You can stay as long as you like or as short, but only if you follow my rules." "You already know my answer Auntie Mary, I have to get away from that bastard." "What about you Mandy?" "Yes please Auntie Mary. I will need to buy lots of stuff just to get started, but yes please." This was perfect, I had thought that it was going to take me a long time to integrate myself into this world but auntie Mary's invitation took me straight there. The big problem would be that I was now going to have to go full time. Kate was not going to like it. "OK, when we have finished breakfast I will take you to my place and get you settled in. you can tell me more about yourselves and I can show you round and explain more of the set up." The rest of breakfast passed in a haze. When we had finished breakfast, Sue and I collected the small amount of belongings that we had and followed Auntie Mary for about half a mile from the club. Mary's place was a Victorian town house spread over a basement, three floors and the attics. Auntie Mary was not hard up. We were shown to a good sized bedroom on the second floor. There were two large single beds and plenty of storage, plus a nice vanity unit and an en suite bathroom. We decided on who would sleep where and put away our few belongings. We then joined Mary in the large basement kitchen and met Daisy, the only other resident who was at home. Daisy was taller than both Sue and myself with fairly broad shoulders. She looked fairly masculine but had a bust and a personality that stuck out a long way. From the cleavage on display, the bust was all hers. She was fun and had us laughing from the outset. She worked in Aunty Mary?s special shop, but had the morning off because she was visiting her psychologist. She told us she was 22 years old and had been in transition for three years, but had not yet had the final stage. She was hoping to have that done in the next six months. We nattered over a cup of coffee until Aunty Mary suggested that I go with Sue to help her collect her stuff from where she had been staying. I was very nervous about going out as I was, but Sue told me that I would be fine. We took the underground across the city to Mile End and went to Sue?s partner?s flat. This was the first time that I had been out to the public dressed as a woman. I was hugely self conscious and convinced that everybody would see me as a guy in drag. Sue was very cautious, when we got to the flat, checking first if he was in. When she realised the coast was clear, we went in to this tip of a place and started filling black bags with her stuff. It took more than half an hour and the two of us were terrified that he would return. When were ready to go, Sue went to the desk draw and took what looked to be about ?500 and put it in her purse. With a sigh of relief we left and locked up. Sue was euphoric and decided that we would get a cab back to Auntie Mary?s. Now that she was safely away from the bastard, she started to tell me the detail of how she had been treated and I started making a mental note of all the men that had been involved. We got back to the house late in the morning and I helped Sue put away all her belongings. They weren?t many, but they made my few outfits and one set of men?s clothes, look very thin. I needed to contact Kate, and let her know that I would not be home, and Sergeant Waters and let her know my current situation. I also needed to give her the names of Sue?s abusers. Mary suggested that I go with her to her special shop and afterwards to go with Sue to purchase enough women?s clothes to get me started. Mary?s shop was a fantasy world. Everything was there for a man to become a woman. There were toys, bits of equipment, outfits, wigs and things that I made a note to ask Mary about. There were consulting rooms where customers could be given a complete makeover. There was even a hair removal service. Mary had me strip naked and examined me. She humed and tutted as she felt my chest, shoulders, waist, bum and my meat and two veg. "Right young Mandy, I think the best place to start is to give you your own breasts. I think a B cup is going to be about right until you start to develop your own and get implants. We can sort that now as soon as I can select a match for your skin colour. I will be taking the cost of these off your wages but that can wait until you have earned enough to get by. Now lie down on the couch while I fix them. Good girl, these will help you adjust to femininity, they will change your balance and make you look much more natural. Lie there for another three minutes, while they set. I think you are going to need a better corset, it will slim your waist, push flesh down to your bum and improve your posture. You also need a proper gaff. Lets get this one on you while your breasts set. Lift your bum. There, that is a lot more snug and gives you a better line. Right, up you get and I will fit this corset on you. It will feel very restricting to start with but it will be worth it. It will be good when you wear your maid?s outfit. Hold on to that pole and breath in when I pull the cords. Good, well done, more, more, more, one more, that will do to start. How do you feel?" "That is bloody tight, I can hardly breath and my ribs hurt. My balance is all wrong with my bust. It is strange. My nuts feel as if they are being crushed." "Just stand and breath and then look in the mirror. What you see will make it worth while." What I saw was my face but the body of a woman. I stood more upright and pulled my shoulders back. The figure looked better now. It was strange to see my body so changed. "Right young lady, get your clothes back on, sort your wig and make up and off you go with Sue to get what you need. When you have finished meet me back here." Sue was delighted to guide me and also take the opportunity to spend some money herself. She was very critical of my wig, eyebrows and skin tone, but thought my bust, my hips and my bum looked better now. She also said that my voice, posture and mannerisms needed work. Her first question was, how much could I afford to spend. When I said that I thought that I could spend up to a thousand pounds to start with, she was ecstatic. She examined my hair which was long for a policeman but short for a girl. One phone call later and I was on my way to a hair salon. Once sat in a chair, my wig was removed and, within an hour, my hair was a sexy pixie cut with extensions and highlights, making my auburn hair glow. The hair style made my cheek bones look sharper and my face less masculine. My brows had been plucked and shaped and I was two hundred and forty five quid poorer. Sue assured me that it was a good investment, because it would tide me over until my own hair was long enough to style. It was a wonderful relief, being free of the wig. My head felt free and light, but I was very conscious of the shiny hair in my peripheral vision. Sue then took me for a whirlwind tour of the sales in London. We started from the inside out. All the while, Sue kept correcting me, when I was too masculine in my speech or actions. It was fun. I was carried away with Sue?s enthusiasm. We bought panties, bras, slips, skirts, blouses, camisoles, one long dress and a couple of summer dresses, jumpers, T shirts, shoes a hand bag, a trendy back pack, a suitcase, tights, stockings, sleepwear, a robe, some belts, ear rings, a bracelet, necklace, rings, make up and a watch. I had really enjoyed the choosing and the trying things on. I had found myself giggling like a schoolgirl with Sue. The fun was infectious. I was actually looking forward to getting a chance to try everything on. I needed to remember that I was a detective, not a giggling schoolgirl. We got back to Mary?s emporium and she showed us round, explaining what the different products were. Some were enough to make my eyes water. "Right you pair, I am going to give you your first instruction on electrolysis and laser hair removal. You Sue can help me as I show you how to work on Mandy?s chin, then Mandy can help me work on your underarms Sue." The next hour was painful and instructional. I was very glad of the soothing cream that took the sting out of my face. At five Mary left her staff to look after the shop and the three of us went back to the house. I was desperate to find an opportunity to talk to Kate and DS Waters. We packed away my spoils from the day, and I told Mary that I thought that I should let a woman friend know where I was and that I was safe. I went outside to call, but Kate?s phone was off. All I could do was leave a long text and then remove it from the memory. I checked the rest of the memory to see if anything might cause suspicion if someone picked up my phone. Next I called DS Waters and brought her up to speed, giving her the names of all Sue?s abusers, with a caution not to go in heavy handed. Mary told Sue and I to prepare dinner for the five of us in the house. It was fun working out what we were capable of preparing between us and checking that against what was available in the larder. Once we had prepared the food, the five of us sat round the big kitchen table and planned our visit to Mac and Mabel?s for the karaoke. With my new stash of clothes, I now had choices. Sue and I went to our room and tried on various outfits. With my corset on, I looked OK in the one cocktail dress that I had bought, a little black number. My thong gaff avoided visible panty line and hold up stockings completed the look. Sue picked a sheath of a dress in pink, which looked great with her honey blond hair. The bust was cut low and a push up bra accentuated Sue?s very own cleavage. Sue was keen to show off her proudest assets. She had started taking hormones secretly from the age of fifteen and had gone through female, rather than male puberty. When we stripped down, she was very interested in my cock, her eyes lit up when she saw it. She showed me her little, boy sized appendage, and told me that she had been castrated when she was seventeen, because the hormones had caused her balls to go sceptic. She was now trying to save enough money to finish her transition. She was about two inches shorter than me and looked like a pretty young woman. There was no way that she would have been seen as male. I thought that she made me look very masculine next to her, but she told me that was just my lack of self confidence. Sue helped me with my make up and I thought that I looked quite passable when we had finished. Mary had booked a cab for Daisy, herself and Sue and I. Sally, the other resident, was working the evening as a maid, so she was not able to come. Mac and Mabel?s was a riot of noise, colour and people. There was a wide mix of Tgirls, crossdressers, women, men, Divas, women dressed as men, transgendered, the androgynous, gay men of all types and shapes and what may or may not have been straight men and women. The bar was throbbing and there were already performers on the stage. The option was either to mime to the song of a well known female singer, or sing to a backing track. I had not come with any intention of singing, but, it looked fun and the audience response was wonderful. I was tempted. I was blessed with a decent singing voice and a vocal range that could cover the full mezzo soprano range. After several shots and a glass of wine I was persuaded to go on stage. I gave it my all. Imitating the most Diva ish of performers. It brought the house down. An encore was demanded and I was asked if I would go back on stage again later. It was a buzz. A little later a very flamboyantly dressed and extravagantly made up, female impersonator came to talk to me. "Hi, let me introduce myself, my name is Dolores Delights. I run the entertainment here and in a number of other establishments. That performance, you gave, was pretty impressive. Do you perform professionally?" "No, you must be joking, that was the first time I have ever sung as a woman. I did sing treble at school and have enjoyed karaoke on drunken nights, but that was a first." "Did you enjoy it?" "God yes, the applause was a buzz." "How do you fancy doing it for money?" "Where, when, how much?" "I have a group of artists who perform at clubs like this, gay bars and private cabarets. There is enough work for my girls to be on stage three or four nights a week. Some work more, some work less. The fees are anything from ?50 a show up to the high hundreds, depending on your skill and the venue. How many songs could you perform as an act?" "I don?t know, I don?t have an act. I suppose that there must be quite a few, but I would have to brush up on the words and tunes. Are all the venues local?" "No, my girls perform all over the country, there are even gigs abroad and on cruise ships. It does not pay mega star money, but the best make a very good living. I would like to give you a proper audition, if you are interested. You have the voice, but your presentation would need working on. You are far too male in your behaviour at the moment. Here is my card. If you are interested, give me a call tomorrow." When I saw Auntie Mary, I asked her about Dolores Delights. "My goodness, you have fallen on your feet Mandy dear. Dolores runs the top group of female impersonators in the country. If you get on her books, you can make a reasonable living from singing alone. It would mean a lot of travel though. I would take her up on the audition, find out more and then make my mind up later." "You lucky cow, I wish I had a voice, I could do the stage strutting and the sexiness, no trouble." "You could certainly do that Sue. If I did decide to go for it, I will need you to coach me how to be sexy." I sang two more songs later and took the road back home to Mary?s on a high. When we went to bed, Sue and I changed into nightdresses, cleaned off make up and moisturised. It was a relief to lose the corset. It was gone midnight and I was exhausted. It had been a very long and full day. So much had changed in a little over 24 hours. "Mandy, I feel sad and lonely. Can I join you for a cuddle. I have not slept on my own for a very long time." "OK, just a cuddle mind." "Thank you Mandy." Sue quickly got into bed with me and snuggled in to me. I was exhausted and quickly fell asleep.